US9454078B2 - Positive-type photosensitive resin composition, method for producing semiconductor device including cured film using the same - Google Patents

Positive-type photosensitive resin composition, method for producing semiconductor device including cured film using the same Download PDF

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US9454078B2
US9454078B2 US14/422,664 US201314422664A US9454078B2 US 9454078 B2 US9454078 B2 US 9454078B2 US 201314422664 A US201314422664 A US 201314422664A US 9454078 B2 US9454078 B2 US 9454078B2
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general formula
structural unit
unit represented
resin composition
weight
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US20150212412A1 (en
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Hiroyuki Onishi
Yuki Masuda
Masao Tomikawa
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Toray Industries Inc
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Toray Industries Inc
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/022—Quinonediazides
    • G03F7/023—Macromolecular quinonediazides; Macromolecular additives, e.g. binders
    • G03F7/0233—Macromolecular quinonediazides; Macromolecular additives, e.g. binders characterised by the polymeric binders or the macromolecular additives other than the macromolecular quinonediazides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1042—Copolyimides derived from at least two different tetracarboxylic compounds or two different diamino compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1046—Polyimides containing oxygen in the form of ether bonds in the main chain
    • C08G73/105—Polyimides containing oxygen in the form of ether bonds in the main chain with oxygen only in the diamino moiety
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1075—Partially aromatic polyimides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1075—Partially aromatic polyimides
    • C08G73/1082—Partially aromatic polyimides wholly aromatic in the tetracarboxylic moiety
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/14—Polyamide-imides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/22—Compounds containing nitrogen bound to another nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/35—Heterocyclic compounds having nitrogen in the ring having also oxygen in the ring
    • C08K5/357—Six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D179/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09D161/00 - C09D177/00
    • C09D179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • C09D179/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/022—Quinonediazides
    • G03F7/0226—Quinonediazides characterised by the non-macromolecular additives
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/26—Processing photosensitive materials; Apparatus therefor
    • G03F7/40—Treatment after imagewise removal, e.g. baking

Definitions

  • the present invention relates to a positive-type photosensitive resin composition, and a method for producing a semiconductor device including a cured film using the same. More particularly, the present invention relates to a positive-type photosensitive resin composition which is suitably used in a surface protective film and an interlayer dielectric film of semiconductor devices, an insulating layer of organic electroluminescence elements, and the like.
  • polyimide-based and polybenzoxazole-based resins having excellent heat resistance and electrical insulation properties have widely been used in a surface protective film and an interlayer dielectric film of semiconductor device, an insulating layer of organic electroluminescence elements, a flattened film of TFT substrates, and the like.
  • a coating film of a polyimide precursor and a polybenzoxazole precursor is thermally cyclodehydrated to obtain a thin film having excellent heat resistance and mechanical properties, firing at a high temperature of about 350° C. is usually needed.
  • a low-temperature curable resin composition includes, for example, a photosensitive resin composition in which a ring-closed polyimide, a photo acid generator, and a heat crosslinking agent having a methylol group are used (Patent Literature 1).
  • the photosensitive resin composition had a problem such as large warpage because of high elastic modulus and high shrinkability during curing.
  • Photosensitive resin compositions in which a polyimide or polybenzoxazole precursor including an aliphatic introduced therein and a photo acid generator are used could achieve low elastic modulus, but film shrinkage due to dehydration ring closure leads to large warpage. Therefore, low warpage could not be realized even in the case of the photosensitive resin compositions in which these resins are used.
  • a water-soluble photosensitive composition comprising a multi-component block copolymerization polyimide resin having an average molecular weight of 20,000 to 200,000, including a specific diamine residue and acid dianhydride residue, a photosensitizer, and water (Patent Literature 4).
  • the water-soluble photosensitive composition has poor exposure sensitivity because of using a material for achieving low linear expansion property and also has restricted uses because of containing a large amount of water, and thus the composition cannot be used in a surface protective film and an interlayer dielectric film of semiconductor devices, an insulating layer of organic electroluminescence elements, and the like.
  • a negative-type photosensitive composition comprising a soluble polyimide including an aliphatic diamine introduced therein, a photopolymerizable compound, and a photopolymerization initiator has been proposed (Patent Literature 5).
  • Patent Literature 5 the negative-type photosensitive composition could not satisfy resolution required for use as a surface protective film of semiconductor devices.
  • An object of the present invention is to provide a positive-type photosensitive resin composition capable of obtaining a polyimide cured film which exhibits low warpage, and also has high sensitivity and high resolution during firing at a lower temperature of 250° C. or lower.
  • the resin composition of the present invention consists of the following constituents.
  • the positive-type photosensitive resin composition includes (a) a polyimide resin including a structural unit represented by the general formula (1) and a structural unit represented by the general formula (2), and (b) a quinonediazide compound, wherein the polyimide resin (a) including a structural unit represented by the general formula (1) and a structural unit represented by the general formula (2) has an imidization ratio of 85% or more, and also a ratio of the structural unit represented by the general formula (1) to the structural unit represented by the general formula (2) is within a range of 30:70 to 90:10:
  • X 1 in the general formula (1) represents a tetracarboxylic acid residue including 1 to 4 aromatic rings
  • Y 1 represents an aromatic diamine residue including 1 to 4 aromatic rings
  • X 2 in the general formula (2) represents a tetracarboxylic acid residue including 1 to 4 aromatic rings
  • Y 2 represents a diamine residue including at least two or more alkylene glycol units in the main chain.
  • the present invention provides a positive-type photosensitive resin composition capable of obtaining a cured film which exhibits low warpage, and also has high sensitivity and high resolution during firing at a lower temperature of 250° C. or lower.
  • the resin composition of the present invention is a positive-type photosensitive resin composition including (a) a polyimide resin including a structural unit represented by the general formula (1) and a structural unit represented by the general formula (2), and (b) a quinonediazide compound, wherein the polyimide resin (a) including a structural unit represented by the general formula (1) and a structural unit represented by the general formula (2) has an imidation ratio of 85% or more, and also a ratio of the structural unit represented by the general formula (1) to the structural unit represented by the general formula (2) is within a range of 30:70 to 90:10:
  • X 1 in the general formula (1) represents a tetracarboxylic acid residue including 1 to 4 aromatic rings
  • Y 1 represents an aromatic diamine residue including 1 to 4 aromatic rings
  • X 2 in the general formula (2) represents a tetracarboxylic acid residue including 1 to 4 aromatic rings
  • Y 2 represents a diamine residue including at least two or more alkylene glycol units in the main chain.
  • the polyimide resin (a) of the present invention includes a structural unit represented by the general formula (1).
  • Y 1 represents an aromatic diamine residue including 1 to 4 aromatic rings, and examples of preferred diamine including Y 1 include hydroxyl group-containing diamines such as bis(3-amino-4-hydroxyphenyl)hexafluoropropane, bis(3-amino-4-hydroxyphenyl)sulfone, bis(3-amino-4-hydroxyphenyl)propane, bis(3-amino-4-hydroxyphenyl)methylene, bis(3-amino-4-hydroxyphenyl)ether, bis(3-amino-4-hydroxy)biphenyl, and bis(3-amino-4-hydroxyphenyl)fluorene; sulfonic acid-containing diamines such as 3-sulfonic acid-4,4′-diaminodiphenylether; thiol group-containing diamines such as dimercaptophenylenediamine
  • the polyimide resin (a) of the present invention also includes a structural unit represented by the general formula (2).
  • Y 2 represents a diamine residue including at least two or more alkylene glycol units in the main chain.
  • the diamine residue is preferably a diamine residue including two or more of one or both of an ethylene glycol chain and a propylene glycol chain in total in a molecule, and more preferably a diamine residue having a structure including no aromatic ring.
  • Examples of the diamine including an ethylene glycol chain and a propylene glycol chain include, but are not limited to, JEFFAMINE (registered trademark) KH-511, JEFFAMINE ED-600, JEFFAMINE ED-900, and JEFFAMINE ED-2003; and examples of the diamine including an ethylene glycol chain include, but are not limited to, JEFFAMINE EDR-148 and JEFFAMINE EDR-176 (which are trade names, manufactured by HUNTSMAN Corporation).
  • X 1 in the general formula (1) represents a tetracarboxylic acid residue including 1 to 4 aromatic rings.
  • X 2 in the general formula (2) represents a tetracarboxylic acid residue including 1 to 4 aromatic rings.
  • X 1 and X 2 may be the same or different.
  • tetracarboxylic acid examples include aromatic tetracarboxylic acids such as pyromellitic acid, 3,3′,4,4′-biphenyltetracarboxylic acid, 2,3,3′,4′-biphenyltetracarboxylic acid, 2,2′,3,3′-biphenyltetracarboxylic acid, 3,3′,4,4′-benzophenonetetracarboxylic acid, 2,2′,3,3′-benzophenonetetracarboxylic acid, 2,2-bis(3,4-dicarboxyphenyl)hexafluoropropane, 2,2-bis(2,3-dicarboxyphenyl)hexafluoropropane, 1,1-bis(3,4-dicarboxyphenyl)ethane, 1,1-bis(2,3-dicarboxyphenyl)ethane, bis(3,4-dicarboxyphenyl)methane, bis(2,3-
  • the polyimide resin (a) of the present invention can be obtained by reacting tetracarboxylic dianhydride serving as a tetracarboxylic acid residue represented by the above-mentioned X 1 and X 2 with diamine serving as a diamine residue represented by the above-mentioned Y 1 and Y 2 to obtain a polyamic acid, and allowing the polyamic acid to undergo dehydration ring closure by a heating treatment, or a chemical treatment with an acid or a base.
  • the polyimide resin (a) of the present invention is characterized in that an imidization ratio is 85% or more, and preferably 90% or more.
  • an imidization ratio is 85% or more, film shrinkage due to dehydration ring closure, which occurs when imidization is performed by heating, decreases and also the occurrence of warpage can be suppressed.
  • the polyimide resin (a) used in the present invention may be composed of only structural units of the general formula (1) and the general formula (2), or may be a copolymer or mixture with other structural units.
  • a ratio of the structural unit represented by the general formula (1) to the structural unit represented by the general formula (2) is within a range of 30:70 to 90:10. The ratio is preferably adjusted within a range of 50:50 to 90:10 since excellent developability is achieved, and more preferably 60:40 to 80:20 since more excellent developability as well as high sensitivity and high resolution are achieved.
  • the structural unit represented by the general formula (1) and the structural unit represented by the general formula (2) preferably accounts for 50% by weight or more, and more preferably 70% by weight or more, of the whole resin.
  • the polyimide resin (a) of the present invention preferably includes a fluorine atom in the structural unit.
  • the fluorine atom imparts water repellency to a surface of a film during alkali development, thus enabling suppression of permeation from the surface.
  • the content of the fluorine atom in the component of the polyimide resin (a) is preferably 10% by weight or more, and preferably 20% by weight or less in view of solubility in an aqueous alkali solution.
  • an aliphatic group including a siloxane structure may be copolymerized.
  • the diamine component include bis(3-aminopropyl)tetramethyldisiloxane, bis(p-aminophenyl)octamethylpentasiloxane, and the like.
  • the main chain terminal of the polyimide resin (a) is preferably blocked with a terminal blocking agent such as a monoamine, an acid anhydride, a monocarboxylic acid, a mono acid chloride compound, or a monoactive ester compound.
  • a terminal blocking agent such as a monoamine, an acid anhydride, a monocarboxylic acid, a mono acid chloride compound, or a monoactive ester compound.
  • diamine components a monoamine is more preferably used.
  • Examples of preferred compound of the monoamine include aniline, 2-ethynylaniline, 3-ethynylaniline, 4-ethynylaniline, 5-amino-8-hydroxyquinoline, 1-hydroxy-7-aminonaphthalene, 1-hydroxy-6-aminonaphthalene, 1-hydroxy-5-aminonaphthalene, 1-hydroxy-4-aminonaphthalene, 2-hydroxy-7-aminonaphthalene, 2-hydroxy-6-aminonaphthalene, 2-hydroxy-5-aminonaphthalene, 1-carboxy-7-aminonaphthalene, 1-carboxy-6-aminonaphthalene, 1-carboxy-5-aminonaphthalene, 2-carboxy-7-aminonaphthalene, 2-carboxy-6-aminonaphthalene, 2-carboxy-5-aminonaphthalene, 2-aminobenzoic acid, 3-aminobenzoic acid, 4-aminobenzoic acid, 4-aminosalicylic acid
  • the diamine residue including at least two or more alkylene glycol units in the main chain represented by Y 2 in the general formula (2) is preferably a diamine residue having a structure represented by the general formula (3).
  • the existence of the diamine residue having a structure represented by the general formula (3) leads to low elastic modulus and small warpage. It is preferable that elongation is improved and also heat resistance is excellent because of the structure having high flexibility.
  • R 1 and R 2 represent a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, a plurality of R 1 (s) in the same residue may be the same or different, and n represents an integer of 2 to 50.
  • the positive-type photosensitive resin composition of the present invention contains a quinonediazide compound (b).
  • the quinonediazide compound (b) include those with sulfonic acid of quinonediazide ester-bonded to a polyhydroxy compound, those with sulfonic acid of quinonediazide sulfoneamide-bonded to a polyamino compound, and those with sulfonic acid of quinonediazide ester-bonded and/or sulfoneamide-bonded to a polyhydroxypolyamino compound.
  • a positive-type photosensitive resin composition which is photosensitive to i-line (wavelength of 365 nm), h-line (wavelength of 405 nm), and g-line (wavelength of 436 nm) of a mercury lamp, which are common ultraviolet rays, can be obtained. All functional groups of these polyhydroxy compound, polyamino compound, and polyhydroxypolyamino compound may not be substituted with quinonediazide, but two or more functional groups per molecule are preferably substituted with quinonediazide.
  • Such a quinonediazide compound is crosslinked with a polyimide resin (a) at a comparatively low temperature within a range from 120° C. to 140° C.
  • this reaction causes decomposition at about 180° C., the reaction does not serve as a thermally crosslinkable compound (c) for easily obtaining a cured film.
  • This reaction enables suppression of collapse of a pattern shape when using in combination with the thermally crosslinkable compound (c) having a comparatively high reaction initiation temperature of about 180° C., followed by formation of a pattern and further heating treatment at 200° C. or higher.
  • polyhydroxy compound examples include, but are not limited to, Bis-Z, BisP-EZ, TekP-4HBPA, TrisP-HAP, TrisP-PA, TrisP-SA, TrisOCR-PA, BisOCHP-Z, BisP-MZ, BisP-PZ, BisP-IPZ, BisOCP-IPZ, BisP-CP, BisRS-2P, BisRS-3P, BisP-OCHP, methylenetris-FR-CR, BisRS-26X, DML-MBPC, DML-MBOC, DML-OCHP, DML-PCHP, DML-PC, DML-PTBP, DML-34X, DML-EP, DML-POP, dimethylol-BisOC-P, DML-PFP, DML-PSBP, DML-MTrisPC, TriML-P, TriML-35XL, TML-BP, TML-HQ, TML-pp-BPF, TML-BPA, TMOM-BP, HML-TPPHBA
  • polyamino compound examples include, but are not limited to, 1,4-phenylenediamine, 1,3-phenylenediamine, 4,4′-diaminodiphenylether, 4,4′-diaminodiphenylmethane, 4,4′-diaminodiphenylsulfone, 4,4′-diaminodiphenyl sulfide, and the like.
  • polyhydroxypolyamino compound examples include, but are not limited to, 2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane, 3,3′-dihydroxybenzidine, and the like.
  • both a 5-naphthoquinonediazidesulfonyl group and a 4-naphthoquinonediazidesulfonyl group are preferably used in quinonediazide.
  • it is also possible to obtain a naphthoquinonediazidesulfonyl ester compound in which a 4-naphthoquinonediazidesulfonyl group and a 5-naphthoquinonediazidesulfonyl group are used in combination in the same molecule and it is also possible to use a 4-naphthoquinonediazidesulfonyl ester compound and a 5-naphthoquinonediazidesulfonyl ester compound as a mixture.
  • the quinonediazide compound (b) contains an ester of a phenol compound and a 5-naphthoquinonediazidesulfonyl group.
  • the quinonediazide compound (b) contains an ester of a phenol compound and a 5-naphthoquinonediazidesulfonyl group.
  • the content of the quinonediazide compound (b) is preferably within a range of 1 to 50 parts by weight, and more preferably 10 to 40 parts by weight, based on 100 parts by weight of the resin as the component (a). An attempt can be made to achieve higher sensitivity by adjusting the content of the quinonediazide compound within the above range. Furthermore, a sensitizer may be optionally added.
  • the positive-type photosensitive resin composition of the present invention may contain (c) a thermally crosslinkable compound for the purpose of easily obtaining a cured film.
  • a thermally crosslinkable compound (c) include a compound having a benzoxazine structure, a compound having an epoxy structure, a compound having an oxetane structure, and a compound having an alkoxymethyl group, and these thermally crosslinkable compounds can also be used as a mixture.
  • a compound having a benzoxazine structure is preferable since degassing due to curing does not occur because of the crossliking reaction due to the ring-opening addition reaction, and also the occurrence of warpage is suppressed because of small shrinkage due to heat.
  • Preferred examples of the compound having a benzoxazine structure include B-a type benzoxazine, B-m type benzoxazine (which are trade names, manufactured by SHIKOKU CHEMICALS CORPORATION), a benzoxazine adduct of a polyhydroxystyrene resin, a phenol novolak type dihydrobenzoxazine compound, and the like. These compounds may be used alone, or two or more of compounds may be mixed.
  • Preferred examples of the compound having an epoxy structure include EPICLON (registered trademark) 850-S, EPICLON HP-4032, EPICLON HP-7200, EPICLON HP-820, EPICLON HP-4700, EPICLON EXA-4710, EPICLON HP-4770, EPICLON EXA-859CRP, EPICLON EXA-4880, EPICLON EXA-4850, EPICLON EXA-4816, EPICLON EXA-4822 (which are trade names, manufactured by Dainippon Ink and Chemicals, Inc.), RIKARESIN (registered trademark) BPO-20E, RIKARESINBEO-60E (which are trade names, manufactured by New Japan Chemical Co., Ltd.), EP-4003S, EP-4000S (which are trade names, manufactured by ADEKA CORPORATION), and the like. These compounds may be used alone, or two or more of compounds may be mixed.
  • Examples of the compound having an oxetane structure include a compound having two or more oxetane rings in a molecule, 3-ethyl-3-hydroxymethyloxetane, 1,4-bis ⁇ [(3-ethyl-3-oxetanyl)methoxy]methyl ⁇ benzene, 3-ethyl-3-(2-ethylhexylmethyl)oxetane, 1,4-benzenedicarboxylic acid-bis[(3-ethyl-3-oxetanyl)methyl]ester, and the like.
  • ARON OXETANE Series manufactured by TOAGOSEI CO., LTD. can be suitably used, and these compounds may be used alone, or two or more of compounds may be mixed.
  • Preferred examples of the compound having an alkoxymethyl group include DML-PC, DML-PEP, DML-OC, DML-OEP, DML-34X, DML-PTBP, DML-PCHP, DML-OCHP, DML-PFP, DML-PSBP, DML-POP, DML-MBOC, DML-MBPC, DML-MTrisPC, DML-BisOC-Z, DML-BisOCHP-Z, DML-BPC, DML-BisOC-P, DMOM-PC, DMOM-PTBP, DMOM-MBPC, TriML-P, TriML-35XL, TML-HQ, TML-BP, TML-pp-BPF, TML-BPE, TML-BPA, TML-BPAF, TML-BPAP, TMOM-BP, TMOM-BPE, TMOM-BPA, TMOM-BPAF, TMOM-BPAP, HML-TPPHBA, HML-TPHAP,
  • the positive-type photosensitive resin composition of the present invention may optionally contain surfactants; esters such as ethyl lactate and propylene glycol monomethyl ether acetate; alcohols such as ethanol; ketones such as cyclohexanone and methyl isobutyl ketone; and ethers such as tetrahydrofuran and dioxane, for the purpose of improving wettability with a substrate.
  • surfactants such as ethyl lactate and propylene glycol monomethyl ether acetate
  • alcohols such as ethanol
  • ketones such as cyclohexanone and methyl isobutyl ketone
  • ethers such as tetrahydrofuran and dioxane
  • the positive-type photosensitive resin composition of the present invention may contain inorganic particles.
  • Preferred specific examples include, but are not limited to, silicon oxide, titanium oxide, barium titanate, alumina, talc, and the like. These inorganic particles preferably have a primary particle diameter of 100 nm or less, and more preferably 60 nm or less.
  • the positive-type photosensitive resin composition of the present invention may contain, as a silicone component, silane coupling agents such as trimethoxyaminopropylsilane, trimethoxyepoxysilane, trimethoxyvinylsilane, and trimethoxythiolpropylsilane, as long as storage stability does not deteriorate.
  • silane coupling agents such as trimethoxyaminopropylsilane, trimethoxyepoxysilane, trimethoxyvinylsilane, and trimethoxythiolpropylsilane, as long as storage stability does not deteriorate.
  • the content of the silane coupling agent is preferably within a range of 0.01 to 5 parts by weight based on 100 parts by weight of the component (a).
  • the positive-type photosensitive resin composition may optionally contain a compound having a phenolic hydroxyl group as long as a shrinkage residual film rate after curing is not decreased. Inclusion of these compounds enables adjustment of a developing time, thus improving scum.
  • the compound having a phenolic hydroxyl group include Bis-Z, BisP-EZ, TekP-4HBPA, TrisP-HAP, TrisP-PA, BisOCHP-Z, BisP-MZ, BisP-PZ, BisP-IPZ, BisOCP-IPZ, BisP-CP, BisRS-2P, BisRS-3P, BisP-OCHP, methylenetris-FR-CR, BisRS-26X (which are trade names, manufactured by Honshu Chemical Industry Co., Ltd.), BIP-PC, BIR-PC, BIR-PTBP, BIR-BIPC-F (which are trade names, manufactured by ASAHI ORGANIC CHEMICALS INDUSTRY CO., LTD.), novolak resin, and the like.
  • the positive-type photosensitive resin composition of the present invention preferably contains a solvent.
  • the positive-type photosensitive resin composition can be put into a state of a varnish, thus improving coatability.
  • solvents for example, polar aprotic solvents such as ⁇ -butyrolactone; ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol mono-n-propyl ether, ethylene glycol mono-n-butyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol mono-n-propyl ether, diethylene glycol mono-n-butyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol mono-n-propyl ether, propylene glycol mono-n-butyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol mono-n-propyl ether, dipropylene glycol monomethyl ether, di
  • the amount of the solvent to be used is not particularly limited and is preferably within a range of 50 to 2,000 parts by weight, and particularly preferably 100 to 1,500 parts by weight, based on 100 parts by weight of the resin as the component (a).
  • the positive-type photosensitive resin composition of the present invention is applied on a substrate.
  • the substrate to be commonly used include, but are not limited to, a silicon wafer, ceramics, gallium arsenide, metal, glass, metal oxide insulating film, silicon nitride, ITO, and the like.
  • the coating method capable of imparting satisfactory in-plane uniformity includes a spin coating method using a spinner, a slit coating method, a method of spin coating after slit coating, a spray coating method, and the like.
  • the thickness of a coating film varies depending on the coating technique, the viscosity and solid content of the composition, and the like, the composition is usually applied so that the film thickness after drying becomes 0.1 to 150 ⁇ m.
  • the substrate coated with the positive-type photosensitive resin composition is dried to obtain a positive-type photosensitive resin composition coating film. Drying is preferably performed at a temperature within a range of 50° C. to 150° C. for one minute to several hours, using an oven, a hot plate, infrared rays, and the like.
  • actinic rays used for exposure include ultraviolet rays, visible rays, electron beams, X-rays.
  • actinic rays selected from i-line (wavelength of 365 nm), h-line (wavelength of 405 nm), and g-line (wavelength of 436 nm) from a mercury lamp are preferably used.
  • the developing solution is preferably an aqueous alkali solution of compounds exhibiting alkalinity, such as tetramethylammonium, diethanolamine, diethylaminoethanol, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, triethylamine, diethylamine, methylamine, dimethylamine, dimethylaminoethyl acetate, dimethylaminoethanol, dimethylaminoethyl methacrylate, cyclohexylamine, ethylenediamine, and hexamethylenediamine.
  • alkalinity such as tetramethylammonium, diethanolamine, diethylaminoethanol, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, triethylamine, diethylamine, methylamine, dimethylamine, dimethylaminoethyl acetate, dimethylaminoethanol, dimethylaminoethyl methacrylate, cyclohexyl
  • polar solvents such as N-methyl-2-pyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, ⁇ -butyrolactone, and dimethylacrylamide
  • alcohols such as methanol, ethanol, and isopropanol
  • esters such as ethyl lactate and propylene glycol monomethyl ether acetate
  • ketones such as cyclopentanone, cyclohexanone, isobutyl ketone, and methyl isobutyl ketone
  • a rinsing treatment is preferably performed using water.
  • the rinsing treatment may also be performed using alcohols such as ethanol and isopropyl alcohol, esters such as ethyl lactate and propylene glycol monomethyl ether acetate, and the like added to water.
  • the film is converted into a heat-resistant resin coating film by heating at a temperature within a range of 100° C. to 400° C. This heating treatment is carried out for 5 minutes to 5 hours such that the temperature is selected and the temperature is elevated stepwise, or a certain temperature range is selected and the temperature is continuously elevated.
  • a heat treatment is performed at 100° C., 150° C., and 250° C. for 60 minutes, respectively, or a heat treatment is performed by linearly elevating the temperature from room temperature to 250° C. over hours.
  • the heat resistance resin coating film formed from the positive-type photosensitive resin composition of the present invention is used, as a cured film, for passivation films of semiconductors, surface protective films in which a cured film of the positive-type photosensitive resin composition is formed on passivation films, interlayer dielectric films formed on circuits of semiconductor devices, insulating layers of organic electroluminescence elements, and the like.
  • the cured film formed from the positive-type photosensitive resin composition of the present invention is a cured film which exhibits low warpage, and also has high sensitivity and high resolution.
  • a positive-type photosensitive resin composition (hereinafter referred to as a varnish) filtered through a 1 ⁇ m thick filter made of polytetrafluoroethylene (manufactured by Sumitomo Electric Industries, Ltd.) in advance was used for evaluation.
  • a solution prepared by dissolving a polyimide resin in N-methylpyrrolidone (NMP) in a solid component concentration of 50% by weight was applied on a 6 inch silicon wafer by a spin coating method, and then baked by a hot plate (SKW-636, manufactured by DAINIPPON SCREEN MFG. CO., LTD.) at 120° C. for 3 minutes to form a prebaked film having a thickness of 10 ⁇ m ⁇ 1 ⁇ m.
  • This film was divided into halves and one half was introduced in an inert oven (INH-21CD, manufactured by Koyo Thermo Systems Co., Ltd.). The temperature was raised to the curing temperature of 350° C. over 30 minutes and then a heating treatment was performed at 350° C. for 60 minutes.
  • a cured film (hereinafter referred to as a “cured film”) was obtained.
  • an infrared absorption spectrum was measured using a Fourier transform infrared spectrophotometer FT-720 (manufactured by HORIBA, Ltd.).
  • a peak intensity at about 1,377 cm ⁇ 1 due to C-N stretching vibration of an imide ring was determined, and a ratio of peak intensity of a cured film (A)/peak intensity of a film (B) before curing was regarded as an imidization ratio.
  • a coating and developing system ACT-8 manufactured by Tokyo Electron Limited
  • application of a varnish on an 8 inch silicon wafer and prebaking at 120° C. for 3 minutes were performed by a spin coating method.
  • an exposure device i-line stepper NSR-2005i9C manufactured by Nikon Corporation
  • exposure was performed.
  • a developing device ACT-8 development with an aqueous 2.38% by weight tetramethylammonium solution (hereinafter referred to as TMAH, manufactured by Tama Chemicals Co., Ltd.) was repeated twice by a paddle method (ejection time of a developing solution of 10 seconds and a paddle time of 40 seconds), followed by rinsing with pure water and further draining and drying.
  • TMAH aqueous 2.38% by weight tetramethylammonium solution
  • sensitivity Minimum light exposure when the exposed area is completely dissolved was regarded as sensitivity.
  • C The case where sensitivity is 500 mJ/cm 2 or more was rated (C) (poor), the case where sensitivity is 300 mJ/cm 2 or more and less than 500 mJ/cm 2 was rated (B) (satisfactory), and the case where sensitivity is less than 300 mJ/cm 2 was rated (A) (more satisfactory).
  • a coating and developing system ACT-8 manufactured by Tokyo Electron Limited
  • application of a varnish on an 8 inch silicon wafer and prebaking at 120° C. for 3 minutes were performed by a spin coating method.
  • a reticle with a cut-off pattern was set in an exposure device an exposure device i-line stepper NSR-2005i9C (manufactured by Nikon Corporation) and the coating film was exposed at an exposure dose of 800 mJ/cm 2 .
  • TMAH aqueous 2.38% by weight tetramethylammonium solution
  • TMAH aqueous 2.38% by weight tetramethylammonium solution
  • a coating and developing system ACT-8 application of a varnish and prebaking at 120° C. for 3 minutes were performed by a spin coating method so that the film thickness after prebaking became 10 ⁇ m.
  • an inert oven CLH-21CD-S manufactured by Kayo Thermo Systems Co., Ltd.
  • the temperature was raised to 200° C. at 3.5° C./minute in the oxygen concentration 20 ppm or less, and a heating treatment was performed at 200° C. for one hour.
  • the wafer was taken out and the cured film was measured using a stress measurement system FLX2908 (manufactured by KLA-Tencor Corporation).
  • TrisP-PA trade name, manufactured by Honshu Chemical Industry Co., Ltd.
  • NAC-5 5-naphthoquinonediazidesulfonic acid chloride
  • a triethylamine salt was filtered off and the filtrate was poured into water. Thereafter, the precipitate thus formed was collected by filtration and washedwith 1 L of aqueous 1% hydrochloric acid. Thereafter, the precipitate was further washed twice with 2 L of water. This precipitate was dried by a vacuum dryer to obtain a quinonediazide compound (B) represented by the following formula.
  • ODPA 3,3′,4,4′-diphenylethertetracarboxylic dianhydride
  • BAHF 2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane
  • 2.5 g (0.01 mol) of 1,3-bis(3-aminopropyl)tetramethyldisiloxane were added together with 250 g of NMP, followed by a reaction at 60° C. for one hour and further reaction at 200° C. for 6 hours.
  • a ratio of a structural unit represented by the general formula (1) to a structural unit represented by the general formula (2) was 68:32, and an imidization ratio was 96%.
  • a ratio of a structural unit represented by the general formula (1) to a structural unit represented by the general formula (2) was 61:39, and an imidization ratio was 91%.
  • This precipitate was collected by filtration, washed three times with water, and then dried by a vacuum dryer at 80° C. for 40 hours to obtain a polyimide precursor (A-3) in which a ratio of a structural unit represented by the general formula (1) to a structural unit represented by the general formula (2) is 68:32, and an imidization ratio is 33%.
  • a ratio of a structural unit represented by the general formula (1) to a structural unit represented by the general formula (2) was 56:44, and an imidization ratio was 98%.
  • the resin (A-1) (100 parts by weight) obtained in the above Synthesis Example, 20 parts by weight of (B), 10 parts by weight of B-m type benzoxazine as the component (c), and 140 parts by weight of gamma-butyrolactone as the solvent were added to prepare a varnish, and then the varnish was evaluated by the above method.
  • the resin (A-1) (100 parts by weight) obtained in the above Synthesis Example, 25 parts by weight of (B), 30 parts by weight of (C) as the component (c), 10 parts by weight HMOM-TPHAP, and 140 parts by weight of gamma-butyrolactone as the solvent were added to prepare a varnish, and then the varnish was evaluated by the above method.
  • the resin (A-1) (100 parts by weight) obtained in the above Synthesis Example, 25 parts by weight of (B), 10 parts by weight of B-m type benzoxazine as the component (c), 10 parts by weight of HMOM-TPHAP, 30 parts by weight of EPICLON EXA-4880, and 170 parts by weight of gamma-butyrolactone as the solvent were added to prepare a varnish, and then the varnish was evaluated by the above method.
  • the resin (A-2) (100 parts by weight) obtained in the above Synthesis Example, 25 parts by weight of (B), 30 parts by weight of (C) as the component (c), 10 parts by weight of HMOM-TPHAP, 30 parts by weight of EPICLON EXA-4880, and 170 parts by weight of gamma-butyrolactone as the solvent were added to prepare a varnish, and then the varnish was evaluated by the above method.
  • the resin (A-2) (100 parts by weight) obtained in the above Synthesis Example, 25 parts by weight of (B), 10 parts by weight of HMOM-TPHAP as the component (c), 30 parts by weight of EPICLON EXA-4880, and 170 parts by weight of gamma-butyrolactone as the solvent were added to prepare a varnish, and then the varnish was evaluated by the above method.
  • the resin (A-1) (100 parts by weight) obtained in the above Synthesis Example, 20 parts by weight of (B), and 140 parts by weight of gamma-butyrolactone as the solvent were added to prepare a varnish, and then the varnish was evaluated by the above method.
  • the resin (A-5) (100 parts by weight) obtained in the above Synthesis Example, 25 parts by weight of (B), 30 parts by weight of (C) as the component (c), 10 parts by weight of HMOM-TPHAP, and 140 parts by weight of gamma-butyrolactone as the solvent were added to prepare a varnish, and then the varnish was evaluated by the above method.
  • compositions of the above evaluation varnishes are shown in Table 1.

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